(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran
• CAS No.: 260411-23-2
• Molecular Formula: C₃₉H₄₀O₆
• Molecular Weight: 604.743

Synonyms:(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran

Chemical Property of (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran

Chemical Property:

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Technology Process of (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran

There total 3 articles about (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

benzyl bromide (100-39-0) + methyl 3-O-NAP-α-D-galactoside (260411-21-0) → (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran (260411-23-2)

Guidance literature:

With potassium hydroxide; 18-crown-6 ether; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(99)02046-8

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran (260411-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 4 h / Heating

1.2: 93 percent / n-Bu₄NI / 18 h / 80 - 85 °C

2.1: 63 percent / KOH; 18-crown-6 / tetrahydrofuran / 12 h / 20 °C

With potassium hydroxide; 18-crown-6 ether; di(n-butyl)tin oxide; In tetrahydrofuran; benzene; 1.1: Metallation / 1.2: Alkylation / 2.1: Alkylation;

DOI:10.1016/S0040-4039(99)02046-8

Reference yield:

methyl α-D-galactopyranoside (3396-99-4) → (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran (260411-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 4 h / Heating

1.2: 93 percent / n-Bu₄NI / 18 h / 80 - 85 °C

2.1: 63 percent / KOH; 18-crown-6 / tetrahydrofuran / 12 h / 20 °C

With potassium hydroxide; 18-crown-6 ether; di(n-butyl)tin oxide; In tetrahydrofuran; benzene; 1.1: Metallation / 1.2: Alkylation / 2.1: Alkylation;

DOI:10.1016/S0040-4039(99)02046-8

upstream raw materials:

benzyl bromide

methyl 3-O-NAP-α-D-galactoside

2-bromomethylnaphthyl bromide

methyl α-D-galactopyranoside

Downstream raw materials:

methyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside

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